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male/male male_humanoid male_penetrated male_penetrating male_penetrating_female male_penetrating_male millie_(helluva_boss) moan monochrome motion_lines moxxie_(helluva_boss) on_back onomatopoeia penetrating_while_penetrated penetration penile penile_penetration penis penis_in_ass penis_in_pussy perineum plap potatonebula pussy_juice_on_penis rear_view sex signature sketch sound_effects spade_tail tail tail_around_balls text threesome thrusting trio underhoof unguligrade vaginal vaginal_fluids vaginal_penetration 1:1 2021 2_horns big_eyes big_horn black_and_white black_text breasts crackers_(qwerty_soda) demon dialogue digital_drawing_(artwork) digital_media_(artwork) english_text eyelashes female gesture hand_gesture handwritten_text hi_res horn monochrome open_mouth open_smile pointing qwerty_soda simple_background sketch smile solo speech_bubble text white_background 2023 2_horns bite_mark bite_mark_on_chest bite_mark_on_neck black_and_white blush blush_lines bottomwear breath bulge bulge_grab chest_lick clothed clothing curved_horn demon demon_humanoid dessert duo eyebrows eyelashes female female_humanoid fingerless_gloves floral_shirt food food_fetish food_play freckled_face freckles gloves hair handwear head_grab helluva_boss horn humanoid humanoid_on_humanoid ice_cream imp intraspecies licking long_eyelashes looking_down male male/female male_humanoid markings millie_(helluva_boss) mole_(marking) monochrome moxxie_(helluva_boss) navel not_furry open_clothing open_shirt open_topwear potatonebula shirt short_hair signature sitting sketch skirt spade_tail striped_horn stripes swimming_trunks swimwear tail teeth tongue tongue_out topwear 2021 animal_humanoid belly black_and_white breasts cat_humanoid circle_eyebrows climbing clock clothed clothing digital_drawing_(artwork) digital_media_(artwork) eyebrows eyelashes eyes_closed fangs felid felid_humanoid feline feline_humanoid female front_view hair hi_res humanoid inner_ear_fluff mammal mammal_humanoid monochrome multiple_poses myre_(qwerty_soda) navel on_one_leg open_mouth pose qwerty_soda sharp_teeth simple_background solo standing tail teeth thick_thighs tuft unusual_anatomy unusual_tail white_background x_navel 2021 2_horns alternate_form animate_inanimate backpack black_and_white boots bottomwear clothing crackers_(qwerty_soda) demon digital_drawing_(artwork) digital_media_(artwork) doll duo eyelashes eyes_closed female fingers footwear hands_on_shoulders heart_symbol hi_res horn human kissy_face lips living_doll living_plushie male male/female mammal monochrome plushie possessed_inanimate possession puckered_lips qwerty_soda seam_(sewing) shoulder_grab simple_background size_difference skirt small_waist smile spade_tail standing_on_object stitch_(sewing) tail white_background 2023 3_toes anal anal_penetration anthro anthro_on_anthro biped black_and_white black_text blush blush_lines bodily_fluids bottomwear breasts butt canid canid_demon canine cheek_tuft clothed clothed/nude clothed_anthro clothed_female clothing collar crop_top demon dialogue digitigrade dildo dildo_in_ass dildo_insertion dominant dominant_female duo english_text eyebrows eyelashes facial_tuft fangs feet female female/female female_anthro female_penetrated flufy_tail foot_fetish foot_play footjob genital_fluids grin hair hellhound helluva_boss holding_leash holding_object hugging_leg humiliation humping intraspecies leaning leaning_backward leaning_forward leash leash_pull leashed_collar long_hair loona_(helluva_boss) mammal medium_breasts midriff monochrome motion_lines mythological_canine mythological_creature mythology nude nude_anthro nude_female object_in_ass penetration potatonebula pussy_juice_on_butt pussy_juice_on_feet queen_bee-lzebub_(helluva_boss) sex sex_toy sex_toy_in_ass sex_toy_insertion sharp_teeth shirt shorts signature sitting sketch smile snout sound_effects speech_bubble spiked_collar spikes spread_legs spreading stuttering submissive submissive_female tail talking_to_another talking_to_partner teeth text toes topwear tuft vaginal vaginal_fluids vaginal_footjob yelling 2023 2_horns 4_fingers anthro avian beak belt bite_mark bite_mark_on_breast bite_mark_on_shoulder bite_mark_on_thigh black_and_white black_text bottomwear bra breasts clothed clothing curved_horn demon demon_humanoid dialogue dressing duo english_text eyebrows eyelashes facial_hair fangs feather_hair feathers female female_anthro fingerless_gloves fingers genitals gloves hair handwear head_tilt helluva_boss holding_clothing holding_object horn humanoid humanoid_on_anthro imp interspecies lingerie long_eyelashes male male/female male_humanoid medium_breasts monochrome mouth_closed mustache navel nipples nude nude_anthro nude_female open_belt open_bottomwear open_clothing open_pants panties pants potatonebula pseudo_hair pussy raised_eyebrow ringed_eyes shirt short_hair signature sketch slim_female smile snout spade_tail spiked_tail spikes spikes_(anatomy) stella_(helluva_boss) striker_(helluva_boss) striped_horn stripes tail talking_to_another talking_to_partner teeth text topwear underwear 2023 2_horns anal anal_knotting anal_penetration animal_dildo animal_sex_toy anthro anthro_penetrating anthro_penetrating_humanoid anus arm_grab avian beak begging big_dom_small_sub black_and_white black_text blush bodily_fluids canine_dildo collar curved_horn demon demon_humanoid dialogue dildo dildo_in_ass dildo_insertion dominant dominant_anthro dominant_female dripping drooling duo english_text eyebrows eyelashes facial_hair feather_hair feathers female female_anthro female_penetrating female_penetrating_male fucked_silly hair half-closed_eyes heart_symbol helluva_boss horn humanoid humanoid_on_anthro humanoid_penetrated imp kneeling knotting larger_anthro larger_female long_eyelashes looking_back male male/female male_humanoid male_penetrated moan monochrome mustache narrowed_eyes object_in_ass open_mouth pegging penetration potatonebula profanity pseudo_hair pupils ringed_eyes saliva saliva_drip saliva_on_tongue saliva_string scar sex sex_toy sex_toy_in_ass sex_toy_insertion sex_toy_penetration sharp_teeth short_hair sitting size_difference sketch slit_pupils smaller_humanoid smaller_male smaller_penetrated snout spade_tail speech_bubble spiked_tail spikes spikes_(anatomy) stella_(helluva_boss) strapon striker_(helluva_boss) striped_horn stripes stuttering submissive submissive_humanoid submissive_male sweat sweaty_face tail tail_around_body talking_to_another talking_to_partner teeth text tongue tongue_out toying_partner 2023 2_horns 4_fingers anthro areola avian bdsm beak belt black_and_white black_text bodily_fluids bottomwear bottomwear_down breasts cellphone clit_torture clitoral clitoral_masturbation clothed clothing contact_onomatopoeia curved_horn demon demon_humanoid dialogue dirty_talk dominant dominant_humanoid dominant_male duo electronics english_text eyebrows eyelashes eyes_closed facial_hair feather_hair feathers female female_anthro fingers genital_fluids genital_torture genitals glans good_girl head_tilt helluva_boss hi_res horn humanoid humanoid_genitalia humanoid_penis imp impact_onomatopoeia jacket kerchief legwear long_eyelashes male male/female male_humanoid masturbation medium_breasts moan monochrome mostly_nude_anthro mostly_nude_female motion_lines mustache navel neckerchief nipple_clamp nipple_fetish nipple_pinch nipple_play nipple_torture nipples onomatopoeia open_belt open_mouth pants pants_down partially_clothed partially_clothed_humanoid partially_clothed_male penile penile_masturbation penis phone phone_sex pillow pinch pinching_clitoris potatonebula precum pseudo_hair pussy_spanking pussy_torture reclining running_makeup running_mascara saliva saliva_on_tongue saliva_string shaking sharp_teeth short_horn signature sketch small_horn sound_effects speech_bubble spread_legs spreading stella_(helluva_boss) striker_(helluva_boss) striped_horn stripes stuttering submissive submissive_anthro submissive_female sweat sweaty_face talking_to_another talking_to_partner teeth text thigh_highs topwear trembling underwear vein veiny_penis whining white_text 2023 2_horns anthro armwear avian balls bdsm beak belt big_dom_small_sub black_and_white black_text blush boots breasts butt chair cleavage cleavage_cutout clothed clothed_anthro clothed_female clothing curved_horn cutout demon demon_humanoid dialogue discarded_pants dominant dominant_anthro dominant_female duo elbow_gloves english_text eyebrows eyelashes eyes_closed facial_hair feather_hair feathers female female_anthro footwear furniture genitals gloves good_boy handwear helluva_boss high_heeled_boots high_heels holding_paddle horn humanoid humanoid_on_anthro imp interspecies larger_anthro larger_female legwear leotard long_eyelashes male male/female male_humanoid medium_breasts monochrome mostly_nude mostly_nude_humanoid mostly_nude_male mustache on_lap over_knee paddle potatonebula pseudo_hair signature sitting size_difference smaller_humanoid smaller_male spade_tail spank_marks spiked_tail spikes spikes_(anatomy) spot_color stella_(helluva_boss) striker_(helluva_boss) striped_horn stripes stuttering submissive submissive_humanoid submissive_male tail tail_feathers tail_grab talking_to_another talking_to_partner text thigh_boots thigh_highs 2023 2_horns 4_fingers all_fours anal anal_masturbation anal_penetration anus arched_back balls black_and_white black_text blush blush_lines bodily_fluids clothing cloven_hooves collar cum cumshot curved_horn daddy_kink demon demon_humanoid dialogue dildo dildo_in_ass dildo_insertion disembodied_hand dripping drooling duo ejaculation english_text erection eyes_closed facial_hair fingerless_gloves fingers flaccid foreskin genital_fluids genitals gloves hair handwear helluva_boss holding_leash holding_object hooves horn humanoid humanoid_genitalia humanoid_penetrated humanoid_penis imp leash leash_pull leashed_collar looking_back lying male male/male male_humanoid male_penetrated male_penetrating male_penetrating_male masturbation moan monochrome mostly_nude mostly_nude_anthro mostly_nude_humanoid multiple_images mustache not_furry nude nude_anthro nude_male object_in_ass on_side partially_retracted_foreskin penetration penile penile_masturbation penis perineum potatonebula pupils rear_view saliva saliva_drip saliva_on_tongue scar sex sex_toy sex_toy_in_ass sex_toy_insertion short_hair sketch slit_pupils smile smirk solo solo_focus spade_tail spiked_tail spikes spikes_(anatomy) striker_(helluva_boss) striped_horn stripes sweat sweaty_face tail tail_grab tail_pull talking_to_another talking_to_partner tears text tongue tongue_out toying_self vibrator vibrator_on_penis 2023 5_fingers all_fours ambiguous_penetration anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro areola avian barbell_piercing bdsm biped black_and_white black_text bodily_fluids breasts breath butt_slap canid cassie_(eziodude98) collar collar_only daddy_kink demon dialogue dirty_talk doggystyle dripping drooling duo ear_piercing ear_ring english_text eyebrows eyelashes feather_hair feathers female female_penetrated fingers from_behind_position genital_fluids good_girl grabbing_sheets heart_symbol helluva_boss holding_leash holding_object interspecies kneeling leash leash_pull leashed_collar long_eyelashes male male/female male_penetrating male_penetrating_female mammal medium_breasts moan monochrome motion_lines nipple_barbell nipple_piercing nipples nude open_mouth panting pecs penetration penile penile_penetration piercing potatonebula prick_ears pseudo_hair pussy_juice_drip pussy_juice_on_leg ring_piercing rough_sex saliva sex side_view signature sketch slap smile smirk snout spank_marks spanking spiral_eyes stella_(helluva_boss) tail tail_motion tailwag talking_to_another talking_to_partner tears text thrusting tongue vaginal_fluids wide_eyed 2023 2_horns all_fours anal anal_penetration anthro anthro_penetrating anthro_penetrating_humanoid arched_back balls biting_sheets black_and_white black_text blitzo_(helluva_boss) blush blush_lines bodily_fluids chaz_(helluva_boss) contact_onomatopoeia curved_horn demon demon_humanoid dialogue doggystyle drooling duo english_text erection eye_roll eyebrows fish foreskin from_behind_position genitals grabbing_sheets helluva_boss horn humanoid humanoid_focus humanoid_genitalia humanoid_on_anthro humanoid_penetrated humanoid_penis imp impact_onomatopoeia interspecies male male/male male_anthro male_humanoid male_penetrated male_penetrating male_penetrating_male marine moan monochrome motion_lines not_furry_focus onomatopoeia partially_retracted_foreskin penetration penile penile_penetration penis penis_in_ass plap potatonebula rough_sex saliva saliva_on_face sex shark sharp_teeth signature sketch solo_focus sound_effects spade_tail stuttering tail tail_around_arm tail_grab tail_motion tailwag talking_to_another talking_to_partner tears teeth text thrusting 2024 ambiguous_gender annoyed black_and_white brass_instrument breadbug crestamorph digital_drawing_(artwork) digital_media_(artwork) duo elemental_creature flora_fauna hi_res looking_at_another looking_back looking_back_at_another monochrome motion_lines musical_instrument nintendo pikmin pikmin_(species) plant playing_music tuba walking wind_instrument 2023 2_horns 4_fingers biped black_and_white bottomwear cleavage_cutout clothed clothing collarbone crop_top crossdressing curved_horn cutout demon demon_humanoid eyelashes femboy fingerless_gloves fingers freckled_face freckles gloves hair half-closed_eyes handwear helluva_boss hi_res horn humanoid imp legwear looking_at_viewer male male_humanoid midriff monochrome moxxie_(helluva_boss) narrowed_eyes navel not_furry pleated_skirt potatonebula shirt short_hair side_view signature sketch skirt solo spade_tail striped_horn stripes tail tail_under_skirt thigh_highs topwear unguligrade 2023 2_horns 4_fingers bdsm black_and_white breath butt butt_slap clothing cloven_hooves demon demon_humanoid dominant dominant_male duo english_text eyelashes eyeliner female female_humanoid fingerless_gloves fingers furgonomics gloves good_girl grabbing_sheets handwear helluva_boss hi_res hooves horn humanoid imp long_eyelashes looking_at_another looking_at_partner lying makeup male male/female male_humanoid millie_(helluva_boss) monochrome moxxie_(helluva_boss) not_furry on_front on_lap panties potatonebula red_text running_eyeliner signature sitting sketch slap smile smirk spank_marks spanking spot_color striped_horn stripes stuttering submissive submissive_female tail tail_grab tail_pull teeth text underwear 2023 2_horns 4_fingers accessory banknote black_and_white blush blush_lines bodily_fluids boots clothed clothing crossdressing cum cum_from_mouth cum_in_mouth cum_inside demon demon_humanoid duo eyebrows eyelashes facial_hair femboy fingerless_gloves fingers footwear garter garter_straps genital_fluids genitals gloves hair half-closed_eyes handwear helluva_boss horn humanoid humanoid_penetrating imp lingerie lying male male/male male_penetrated male_penetrating male_penetrating_male money monochrome mustache narrowed_eyes not_furry on_side oral oral_penetration penetration penile penile_penetration penis penis_in_mouth potatonebula prostitution pupils ringed_eyes sex short_hair signature sketch slit_pupils solo_focus spade_tail spiked_tail spikes spikes_(anatomy) striker_(helluva_boss) striped_horn stripes tail teddy_(clothing) vein veiny_penis 2023 2_horns 4_fingers barefoot black_and_white blitzo_(helluva_boss) bow_tie calvin_mcmurray clothing cloven_hooves cosplay crossover crossover_cosplay demon demon_humanoid eyebrows feet female female_humanoid fingerless_gloves fingers footwear front_view gloves group gun hair hand_on_hip handwear hat headgear headwear helluva_boss holding_gun holding_object holding_ranged_weapon holding_weapon hooves horn humanoid imp ivy_pepper jacket lackadaisy looking_at_viewer male male_humanoid millie_(helluva_boss) monochrome moxxie_(helluva_boss) necktie not_furry plant potatonebula ranged_weapon rocky_rickaby rolled_up_sleeves shoes short_hair shovel sketch smile smirk standing striped_horn stripes submachine_gun suit thompson_gun tools topwear trio unguligrade vest weapon 2023 2_horns 4_toes all_fours anal anal_penetration anthro anthro_penetrated avian balls beak bird bisexual_parallel_sex black_and_white blitzo_(helluva_boss) breasts contact_onomatopoeia curtains curved_horn demon demon_humanoid dildo dildo_in_ass dildo_insertion doggystyle dominant dominant_female dominant_humanoid dominant_male english_text eyebrows eyelashes eyes_closed feathers feet female female_humanoid female_penetrating female_penetrating_male from_behind_position from_front_position genitals glans grabbing_both_legs group hair hand_behind_head hand_on_face head_grab helluva_boss hooves horn humanoid humanoid_genitalia humanoid_on_anthro humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_anthro humanoid_penetrating_humanoid humanoid_penis imp impact_onomatopoeia inside interspecies intraspecies larger_anthro larger_male larger_penetrated leaning leaning_forward leg_grab long_eyelashes looking_down male male/female male/male male_anthro male_humanoid male_penetrated male_penetrating male_penetrating_male markings millie_(helluva_boss) mole_(marking) monochrome motion_lines mounting moxxie_(helluva_boss) object_in_ass onomatopoeia open_mouth owl owl_demon parallel_sex partner_swap pegging penetration penile penile_penetration penis penis_in_ass plap potatonebula sex sex_toy sex_toy_in_ass sex_toy_insertion sex_toy_penetration short_hair shoulder_stand signature size_difference sketch small_breasts small_dom_big_sub smaller_female smaller_humanoid smile smirk sound_effects spade_tail standing stolas_(helluva_boss) strapon striped_horn stripes submissive submissive_anthro submissive_humanoid submissive_male tail tail_grab teeth text thrusting toes tongue toying_partner unguligrade white_text 2023 2_horns 4_eyes 4_fingers anal anal_penetration anthro anthro_penetrated bent_over black_and_white black_text blush blush_lines bottomwear bottomwear_down bovid breasts caprine caprine_demon cellphone clothed clothing curved_horn demon dialogue dress duo electronics english_text faceless_character faceless_male female female_anthro female_focus female_penetrated fingers goat_demon half-closed_eyes helluva_boss holding_cellphone holding_object holding_phone holding_smartphone horn leaning_on_object male male/female male_penetrating male_penetrating_female mammal monochrome muffy_(helluva_boss) multi_eye narrowed_eyes nurse nurse_clothing oblivious panties panties_down partially_clothed penetration penile penile_penetration penis_in_ass phone potatonebula sex shoulder_grab signature sketch small_breasts smartphone snout solo_focus speech_bubble talking_to_another talking_to_partner text underwear underwear_down 2023 2_horns 4_fingers anal anal_penetration arched_back bite black_and_white black_text blush blush_lines bodily_fluids breath cloven_hooves contact_onomatopoeia cum cumshot curved_horn cutaway demon demon_humanoid dildo dildo_in_ass dildo_insertion duo ejaculation english_text eyebrows eyes_closed facial_hair fingers genital_fluids genitals glans growling hair handjob helluva_boss hooves horn humanoid humanoid_genitalia humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid humanoid_penis imp impact_onomatopoeia intraspecies looking_at_another looking_at_partner lying male male/male male_humanoid male_penetrated male_penetrating male_penetrating_male moan monochrome moxxie_(helluva_boss) mustache not_furry nude nude_humanoid nude_male object_in_ass on_front onomatopoeia panting penetration penile penis pillow pillow_bite plap potatonebula reach_around sex sex_toy sex_toy_in_ass sex_toy_insertion short_hair signature sketch smile smirk sound_effects spade_tail striker_(helluva_boss) striped_horn stripes tail talking_to_another talking_to_partner text toying_partner 920london accessory alternative_fashion anthro black_and_white bodily_fluids bow_ribbon bracelet canid canine clothed clothing crown emo eyewear glasses hair hair_accessory hair_bow hair_ribbon hana_venom headgear hi_res image_comics jewelry line_art mammal monochrome necklace one_eye_closed pawpads ponytail remy_boydell ribbons shirt skull_symbol smile solo sweat sweatdrop tiara topwear 2023 2_horns 4_fingers all_fours anthro anthro_penetrated areola bed bedroom bite biting_lip biting_own_lip black_and_white black_text blush blush_lines bodily_fluids breast_fondling breast_play breasts breeding_kink butt canid canid_demon canine clothing collar collar_only cuckquean curved_horn cutaway daddy_kink demon demon_humanoid dialogue doggystyle dominant dominant_humanoid dominant_male end_table english_text eye_roll eyebrows eyelashes female female_anthro female_humanoid female_penetrated fingering fingering_self fingerless_gloves fingers fondling from_behind_position fur furniture gloves group hair hair_grab half-closed_eyes hand_on_breast handwear head_back headboard hellhound helluva_boss horn humanoid humanoid_on_anthro humanoid_penetrating humanoid_penetrating_anthro imp inside interspecies lamp larger_anthro larger_female larger_penetrated legwear long_eyelashes long_hair loona_(helluva_boss) male male/female male_humanoid male_penetrating male_penetrating_female mammal markings masturbation medium_breasts millie_(helluva_boss) mole_(marking) monochrome mostly_nude_anthro mostly_nude_female mostly_nude_humanoid mostly_nude_male moxxie_(helluva_boss) mythological_canine mythological_creature mythology narrowed_eyes nipples nude on_bed penetration penile penile_penetration penis_in_pussy pillow potatonebula prick_ears pulling_hair reclining rough_sex sex short_hair signature size_difference sketch small_dom_big_sub smaller_humanoid smaller_male smile smirk snout spade_tail spiked_collar spikes striped_horn stripes submissive submissive_anthro submissive_female tail tail_grab talking_to_another talking_to_partner tears teeth text thigh_highs tongue tongue_out tooth_gap touching_hair trio vaginal vaginal_fingering vaginal_masturbation vaginal_penetration voyeur 2023 2_horns balls black_and_white black_text clothed clothing clothing_lift cloven_hooves crossdressing curved_horn demon demon_humanoid dress dress_lift english_text eyebrows femboy fingerless_gloves fishnet_clothing fishnet_legwear genitals glans gloves hair handwear hearts_around_head helluva_boss high-angle_view hooves horn humanoid humanoid_genitalia humanoid_penis imp legwear looking_at_genitalia looking_at_own_penis looking_at_penis looking_at_self looking_down lying male male_humanoid masturbation moan monochrome moxxie_(helluva_boss) no_underwear not_furry on_back penile penile_masturbation penis potatonebula short_hair signature sketch solo spade_tail tail text unguligrade 2_horns 4_fingers biped bite biting_lip biting_own_lip black_and_white black_text bodily_fluids cloven_hooves curved_horn demon demon_humanoid duo embrace english_text entwined_tails eye_roll eyebrows eyes_closed facial_hair fingers genital_fluids genitals glans growling hair half-closed_eyes helluva_boss hooves horn humanoid humanoid_genitalia humanoid_on_humanoid humanoid_penis imp intraspecies lying lying_on_another male male/male male_humanoid monochrome motion_lines moxxie_(helluva_boss) mustache narrowed_eyes not_furry on_back penis potatonebula precum sex sharp_teeth short_hair shoulder_bite signature sketch sound_effects spiked_tail spikes spikes_(anatomy) striker_(helluva_boss) tail tail_coil teeth text thigh_sex thrusting unguligrade 2023 2_horns black_and_white blush blush_lines bottomwear clothed clothing crop_top crossdressing curved_horn demon demon_humanoid erection erection_under_clothing erection_under_skirt femboy hair 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